A funny, entertaining little documentary about quite a character, "Cowboy Del Amor" follows 60-year-old "Cowboy Cupid" Ivan Thompson as he takes men looking for marriage into Mexico to find women. Considered (by himself) to be the best at making matches between American men and Mexican women, he charges $3K to accompany the men down to Mexico, reels in some potential candidates by placing advertisements (with specifics on what the client is looking for) in local newspapers and provides a translator to help the communication between the potential mates, if needed. He also counsels the client, scolding one after he starts talking about his ex-wife to a potential mate.

While Ivan himself has not exactly had the greatest track record when it comes to marriage (he's been divorced more than once and claims that American women are too difficult), he has made successful matches, and one woman comes forward to discuss her current situation. While Thompson gets plenty of hate mail, he actually responds to each and every one, reading one particular letter in front of the camera, as well as his response.

While Thompson has been making matches like this for more than a decade, the film profiles a few clients, including: Rick, a long-distance truck driver who's divorced and the other is James, a glum used car salesman who's been through multiple divorces and looks as if he's seen better days. While one questions why they couldn't find anyone closer to where they live, both seem as if they've been through bad relationships and wanted to look elsewhere for something different.

While many likely have negative opinions on the whole enterprise (and Thompson does seem to get his share of hate mail), filmmaker Michele Ohayon's documentary doesn't judge, even when Ivan offers some dated, misogynistic views. Despite his flaws, he is still a fascinating, occasionally funny character (he has his own set of phrases, called "Ivanisms" in the DVD's extras section) that remains unpredictable. The women who Ivan manages to attract with his service are educated (some college educated, including one dermatologist) and, in every instance here, better educated than the client who's meeting them.

As for the relationships that result of these "matches", there are moments when chemistry is apparent, but others are unsettling and awkward. We see the first morning together with one of the women and her new husband, and while she puts on a brave face, she's looks as if she feels more alone than ever, in a house with a man she barely knows. Interestingly enough, one year later they've actually made a match and seem to be getting along well. Some matches, however, don't work out (and Ivan doesn't offer any 30-day guarantee.) Many of the men appear to be looking for someone who will be subservient to them, whether they're straightforward about it or not.

Ohayon's film keeps the pace moving and doesn't wear out its welcome at just under 90 minutes. While this is a low budget picture, Ohayon has a great cinematographer in Theo van de Sande (also the film's exec producer), who gives the film a more crisp, professional appearance than a low-budget documentary like this may have had otherwise (parts of the film are shot in HD, while others are shot in digital video.)

I don't agree with what Ivan does and felt some of the scenes in the film were cringe-worthy, but "Cowboy Del Amor" doesn't judge and presents a compelling and look at the self-proclaimed king of one particular brand of matchmaking.